Search Holiday Homes in Bailey Island

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Bailey Island Holiday Homes

Our top choices for Bailey Island holiday homes

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (3)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
The price is £372
includes taxes & fees
9 Sept - 10 Sept
Orchid Harbor, Bailey Island 3BR

Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

7.6 out of 10, Good, (13)
"Clean, well maintained, slighly funky in an historical way . Very convenient to great breakfast spots and downtown Bath. Would stay there again."
The price is £124
includes taxes & fees
24 Aug - 25 Aug
Captain's Quarters Guest Room w/Private Bath & Entrance. Best Value in Town!

Private Entrance Residential Portland

8.8 out of 10, Excellent, (3)
"Check in was simple. Quaint place. "
The price is £182
includes taxes & fees
24 Aug - 25 Aug
Private Entrance Residential Portland

Captain's Quarters 1BR Apartment. Walk to everything.

7.8 out of 10, Good, (8)
"Very nice cozy place to make home base for a week. Had everything I needed and owner was very responsive with all of my questions. Primary destination was Bath and very convenient to everything I needed. Thank you!"
The price is £132
includes taxes & fees
25 Aug - 26 Aug
Captain's Quarters 1BR Apartment. Walk to everything.

Bluebird Ocean Point | Deluxe King | Private Beach + Near Grimes Cove Beach

10.0 out of 10, Exceptional, (1)
"The restaurant at the property is amazing. Loved our bartender and our waitress Emma was amazing. She went above and beyond to make our evening unforgettable. We will definitely be back My only complaint is when booking it looks like you are getting a small cabin. But they are actually normal hotel rooms. "
The price is £234
includes taxes & fees
7 Sept - 8 Sept
Bluebird Ocean Point | Deluxe King | Private Beach + Near Grimes Cove Beach

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is £210
includes taxes & fees
15 Sept - 16 Sept
Willard Beach–Private Apt Near Portland & Parks

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is £283
includes taxes & fees
7 Sept - 8 Sept
Sauna & fire table near Portland's Back Cove

30 Acres with Woodland Trails and Playground

2.0 star property
10.0 out of 10, Exceptional, (1)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
30 Acres with Woodland Trails and Playground

Charming Studio apartment with WiFi, AC in welcoming Portland

9.6 out of 10, Exceptional, (5)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is £174
includes taxes & fees
9 Sept - 10 Sept
Charming Studio apartment with WiFi, AC in welcoming Portland

Mid Coast Getaway w/ water views

9.0 out of 10, Wonderful, (2)
"You couldn’t ask for a better view, it was everything we had hoped and more."
The price is £260
includes taxes & fees
24 Aug - 25 Aug
Mid Coast Getaway w/ water views

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is £216
includes taxes & fees
15 Sept - 16 Sept
Camp Forever cottage

Studio Unit Walkable Everywhere

8.0 out of 10, Very good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is £158
includes taxes & fees
7 Sept - 8 Sept
Studio Unit Walkable Everywhere

Full sized home

9.8 out of 10, Exceptional, (34)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is £275
includes taxes & fees
3 Sept - 4 Sept
Full sized home

The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

10.0 out of 10, Exceptional, (1)
"We had a fantastic stay at this peaceful oceanside property in Harpswell, Maine. The setup—with a main house, attached apartment, and a charming bunkhouse—was perfect for our two families and adult children. There was plenty of space for everyone to relax and unwind.The backyard is absolutely stunning, filled with beautiful flowers and lush grass, and it opens up to a tranquil ocean inlet. We especially loved the hammock spot, perfect for a good book or an afternoon nap, and the back porch...
The price is £1,136
includes taxes & fees
21 Sept - 22 Sept
The Harpswell House-Waterfront, SunRise, Big Yards, Classic & Luxury

Beautiful 3BR Home with Office in Town of Brunswick with King beds

9.2 out of 10, Wonderful, (5)
"Had a great stay here, the property was clean and came as advertised"
The price is £422
includes taxes & fees
25 Aug - 26 Aug
Beautiful 3BR Home with Office in Town of Brunswick with King beds

Escape to Positive Outlook

The price is £263
includes taxes & fees
8 Sept - 9 Sept
Escape to Positive Outlook

Downtown Boothbay Harbor, 2-Story Cottage

9.4 out of 10, Exceptional, (22)
"Loved how walkable this property is! "
The price is £235
includes taxes & fees
7 Sept - 8 Sept
Downtown Boothbay Harbor, 2-Story Cottage

Coastal Escape | Hot Tub Fire Pit Chef Kitchen

9.4 out of 10, Exceptional, (3)
"Really nice place. Beds are comfortable. Had nice hot tub with propane fire. Lovely back patio. "
The price is £531
includes taxes & fees
8 Sept - 9 Sept
Coastal Escape | Hot Tub Fire Pit Chef Kitchen

Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

9.0 out of 10, Wonderful, (64)
"We stayed in October when the trees were gorgeous and the dome house is nestled in a wooded area. So pretty! Lots of room for everyone. Wish we could have stayed longer."
The price is £326
includes taxes & fees
15 Sept - 16 Sept
Geodesic Dome w/ Riverfront Deck, Lovely Views, & High-Speed WiFi - Dogs Welcome

Welcome to Owl House - Your Coastal Retreat in East Boothbay!

10.0 out of 10, Exceptional, (5)
"Spacious and comfortable home with open floor plan. We really enjoyed our walks everyday - two blocks from crashing waves, pine trees and steps from the courts and field. It feels remote uniquely beautiful place, yet it is so convenient to stores and restaurants in Boothbay Harbor."
The price is £520
includes taxes & fees
23 Aug - 24 Aug
Welcome to Owl House - Your Coastal Retreat in East Boothbay!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Bailey Island Hotel Reviews